phenyl 6-deoxy-1-thio-β-L-galactopyranoside | 187233-24-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 6-deoxy-1-thio-β-L-galactopyranoside
• 英文别名: phenyl 1-thio-β-L-fucopyranoside；Phenyl 1-thio-beta-l-fucopyranoside；(2S,3S,4R,5S,6R)-2-methyl-6-phenylsulfanyloxane-3,4,5-triol
• CAS: 187233-24-5
• 化学式: C₁₂H₁₆O₄S
• 分子量: 256.323
• InChiKey: YBOVKFRFMWFKCC-VSYPEIIYSA-N

物化性质

• 熔点：
  59-161 °C
• 沸点：
  446.6±45.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  95.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  phenyl 6-deoxy-1-thio-β-L-galactopyranoside 在 碘 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 methyl 2,3,4-tri-O-benzyl-α-L-fucopyranoside
  参考文献：
  名称：

  Control of disaccharide conformation by π-stacking

  摘要：

  一系列衍生物的构象，包括葡萄糖二糖α-L-岩藻糖苷-(1[Formula: see text]3)-2-乙酰胺基-2-脱氧-D-葡萄糖苷的部分，即Le^x决定因子，通过使用MM3*力场进行分子建模和¹H NMR光谱学进行了研究。在苯基2,3,4-三-O-苄基-α-L-岩藻糖苷-(1[Formula: see text]3)-2-脱氧-2-邻二甲酰亚胺基-1-硫-α-D-葡萄糖苷的¹H NMR谱中观察到异常屏蔽的O-苄基质子，并将其归因于2-O-苄基团。这一观察结果可以解释为由于邻二甲酰亚胺和2-O-苄基苯环之间的π-堆积引起的关于糖苷键的构象混合体中的构象种群从未取代的二糖中的正Ψ区域向负Ψ区域的转变。实验核Overhauser增强证实了计算的准确性。关键词：二糖、构象、π-堆积、Le^x决定因子、NOE测量、MM3计算。

  DOI：

  10.1139/v03-062
• 作为产物：
  描述：

  2,3,4-三-O-乙酰基-6-脱氧-alpha-L-溴代半乳糖 在 氢氧化钾 、 sodium methylate 作用下， 以 甲醇 、 乙醇 、 乙酸乙酯 、 丙酮 为溶剂， 反应 14.0h， 生成 phenyl 6-deoxy-1-thio-β-L-galactopyranoside
  参考文献：
  名称：

  Synthesis of Lewis X trisaccharide analogues in which glucose and rhamnose replace N-acetylglucosamine and fucose, respectively

  摘要：

  Two analogues of the Le(x) trisaccharide, alpha-L-Fucp -(1 --> 3)-[beta-D-Galp -(1 --> 4)]-D-Glcp were synthesized as allyl glycosides. In these derivatives either only the N-acetylglucosamine is replaced by glucose or both the N-acetylglucosamine and the facosyl residue are replaced by glucose and rhamnose, respectively. Our synthetic scheme used armed beta-thiophenyl fuco- and rhamnoside glycosyl donors that were prepared anomerically pure from the corresponding alpha-glycosyl bromides. The protecting groups were chosen to allow access to the fully deprotected trisaccharides without reduction of the allyl glycosidic group. These analogues will be used as soluble antigens in binding experiments with anti-Le(x) antibodies and can also be conjugated to a carrier protein and used as immunogens. In the course of this synthetic work, we also describe the use of reversed-phase HPLC to purify key protected trisaccharide intermediates prior to their deprotection. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00053-3

文献信息

• METHOD OF SYNTHESIZING SUGAR CHAIN
  申请人：MITSUBISHI CHEMICAL CORPORATION

  公开号：EP1640379A1

  公开（公告）日：2006-03-29

  An object of the present invention is to provide a method for efficiently chemically synthesizing biomolecules including a nucleotide (nucleic acid), a peptide (protein), or a sugar chain, as representative examples. The present invention provides a method of solid-phase synthesis of sugar chain(s) for synthesizing multiple types of sugar chains in at least one sugar chain synthesis reaction system comprising multiple types of monosaccharide units, which is characterized in that it comprises changing the temperature in the sugar chain synthesis reaction system depending on the temperature rising rate that has been determined based on a decrease in side reaction(s) in the reaction system as an indicator.

  本发明的目的是提供一种有效地化学合成生物分子的方法，包括核苷酸（核酸）、肽（蛋白质）或糖链等代表性示例。本发明提供了一种固相合成糖链的方法，用于在至少一个糖链合成反应系统中合成多种类型的糖链，其特征在于根据已确定的反应系统中副反应减少的指标，改变糖链合成反应系统中的温度上升速率。
• Preparation of Thiosugars and Their Use
  申请人：Davis Benjamin Guy

  公开号：US20090176970A1

  公开（公告）日：2009-07-09

  A process for the preparation of a thiosaccharide represented by Saccharide-S-H wherein Saccharide comprises at least 4 sugar units, comprises subjecting a corresponding compound of the formula (P)Saccharide-S-(P) wherein (P) represents an O- or S-protecting group(s), to Birch reduction.

  一种制备由糖硫代糖（Saccharide-S-H）表示的硫代糖的方法，其中糖代表至少4个糖单元，包括将具有以下结构的相应化合物（P）糖硫代糖（P）进行桦还原：（P）糖硫代糖（P），其中（P）代表一个或多个O-或S-保护基。
• Sulfinyl hexose derivatives useful for glycosylation
  申请人：The Trustees of Princeton University

  公开号：US06040433A1

  公开（公告）日：2000-03-21

  Hexose derivatives are described which facilitate control over the stereochemistry of the glycosyl bond formed in the course of a solid phase glycosylation reaction. Methods for their use are also described.

  描述了一种帮助控制固相糖基化反应过程中形成的糖苷键立体化学的己糖衍生物。还描述了它们的使用方法。
• Regioselective Glycosylation of Unprotected Phenyl 1-Thioglycopyranosides with Phenylboronic Acid as a Transient Masking Group
  作者：Thomas Hauch Fenger、Robert Madsen

  DOI：10.1002/ejoc.201300723

  日期：2013.9

  A useful protocol is described for the regioselective glycosylation of the secondary alcohols in unprotected glycosyl acceptors. Phenyl 1-thioglycopyranosides derived from D-glucose, D-galactose, D-glucosamine, L-rhamnose, and L-fucose were treated with phenylboronic acid to install a temporary boronic ester, and then submitted to a Koenigs–Knorr glycosylation with perbenzoylated glucopyranosyl or galactopyranosyl

  描述了一个有用的协议，用于在未保护的糖基受体中对仲醇进行区域选择性糖基化。衍生自 D-葡萄糖、D-半乳糖、D-葡萄糖胺、L-鼠李糖和 L-岩藻糖的苯基 1-硫代吡喃糖苷用苯基硼酸处理以安装临时硼酸酯，然后用过苯甲酰化吡喃葡萄糖基进行 Koenigs-Knorr 糖基化或吡喃半乳糖基溴化物。与葡萄糖苷和半乳糖苷的 3-位偶联获得了良好的产率，但其他受体的产率较低。使用苯基 1-硫代-β-D-吡喃葡萄糖苷，也可以通过超臂硫代半乳糖苷供体实现偶联。来自葡萄糖-葡萄糖偶联的产物可以在 6 位进行第二次区域选择性糖基化。在半乳糖系列中，
• Total synthesis of trifluorobutyryl-modified, protected sialyl Lewis X by a convergent [2+2] approach
  作者：Gizem Akçay、John Y. Ramphal、Marc d’Alarcao、Krishna Kumar

  DOI：10.1016/j.tetlet.2014.11.029

  日期：2015.1

  adhesion of mammalian cells to E and P-Selectin, presumably by leading to the expression of fluorinated sLex epitopes on cell surfaces, and interfering with the sLex–selectin interactions that are well known in mediating tumour cell migration (J. Med. Chem. 2010, 53, 4277). For studies directed towards understanding the molecular basis of this reduced adhesion, chemical synthesis of trifluorobutyrylated

  真核细胞表面唾液酸残基表达的结构和数量变化深刻影响着广泛的生物学过程，包括炎症，抗原识别，微生物附着和肿瘤转移。唾液酸类似物的摄取和在哺乳动物细胞中的掺入可以进行结构功能研究和特定识别事件的扰动。我们的小组最近表明，三氟丁酰修饰的唾液酸代谢产物可降低哺乳动物细胞对E和P-选择素的粘附力，大概是通过导致细胞表面上氟化的sLe x表位的表达，并干扰sLe x-选择素的相互作用。在介导肿瘤细胞迁移中众所周知的（J.Med.Chem。 2010，53，4277）。对于旨在理解这种降低的粘附力的分子基础的研究，三氟丁酰化唾液酸路易斯X（C 4 F 3 -sLe x）的化学合成至关重要。我们已经开发了一种高效的[2 + 2]方法，可用于制备规模的C 4 F 3 -sLe x，该方法包含通用的保护基，可以根据生物物理研究的需要，将聚糖表面固定或增溶，以研究选择素的相互作用。 。原则上，该策略可用于制备其他N-修饰的sLe